Hydrochloric Acid → Ethyl 4-[bis(phenylmethyl)amino]cyclohexanecarboxylate

HRID 1355587ノート

反応式

HRID 1355587 の反応式
O=[C:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH2:13]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].Cl.[OH-].[Na+]>ClCCCl>[CH2:21]([N:20]([CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:4][CH2:3]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 7656DibenzylamineHCID 14798Sodium HydroxideHCID 317638Ethyl 4-oxocyclohexanecarboxylateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 22287000Ethyl 4-[bis(phenylmethyl)amino]cyclohexanecarboxylate収率 87.9%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a solution of ethyl 4-oxocyclohexanecarboxylate (1.9 g, 11 mmol) in 1,2-dichloroethane (113 mL) at 23° C. was added dibenzylamine (3.4 g, 3.3 mL, 17 mmol) in one portion. After 10 min, sodium triacetoxyborohydride (4.81 g, 22.7 mmol) was added, and the resulting cloudy suspension was stirred for 48 hrs. The suspension was poured into 1N aqueous hydrogen chloride (100 mL), the resulting mixture was basified to pH 9.0-10.0 with 12.5 M aqueous sodium hydroxide. The basic layer was extracted with ethyl acetate (3×50 mL), and the combined organic layers were washed with saturated aqueous sodium chloride (70 mL), dried over sodium sulfate, and concentrated in vacuo. The resulting residue was purified by flash chromatography (5-10% ethyl acetate in hexanes) to yield ethyl 4-(N,N-dibenzylamino)cyclohexanecarboxylate (3.4 g, 84%) as a clear oil. MS (ESI) 352 (M+H).

後処理

  1. extractionThe basic layer was extracted with ethyl acetate (3×50 mL)
  2. washthe combined organic layers were washed with saturated aqueous sodium chloride (70 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography (5-10% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-dafe6227b9424079a0dd7cc7b28e2328
出典データセット
uspto-grants-2003_07
特許番号
US06586446B1

反応ノート

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